Topiramate supplier | CasNO.97240-79-4

Name
Topiramate
EINECS 200-659-6
CAS No. 97240-79-4
Article Data24
CAS DataBase
Density 1.336 g/cm³
Solubility DMSO Solubility : ~44 mg/mL
Melting Point 125 °C
Formula C₁₂H₂₁NO₈S
Boiling Point 438.7 °C at 760 mmHg
Molecular Weight 339.367
Flash Point 219.1 °C
Transport Information
Appearance white to off-white crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms McN-4853;Epitomax;2,3:4,5-bis-o-(1-methylethylidene)-beta-d-fructopyranos sulfamate;a-D-Fructopyranose,2,3:4,5-bis-O-(1-methylethylidene)-,sulfamate;Tipiramato [Spanish];Topamax;Topiramate [USAN:BAN:INN];2,3:4,5-Bis-O-(1-methylethylidene)-beta-D-fructopyranose sulfamate;beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate;Topiramate;Topamax;RWJ-17021-000;2,3:4,5-Di-O-isopropylidene-beta-D-fructopyranose sulfamate;Topiramate (JAN/USAN);Tipiramate [French];Topamax (TN);
PSA 123.92000
LogP 1.38570

Synthetic route

: 150609-95-3
2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With ammonia In tetrahydrofuran; hexane at 20℃; for 3h; Solvent; Temperature;	96.7%
With ammonia In tetrahydrofuran; Petroleum ether at 20℃; for 3h; Solvent;	95.2%
With pyridine; SULFAMIDE In 5,5-dimethyl-1,3-cyclohexadiene at 128 - 133℃; for 3h;	91.1%

: C15H26N2O8S

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With hydrazine hydrate In ethanol at 20℃; for 1h;	90%

: 20880-92-6
2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With pyridine; 2,2,2-trifluoro-1-(trifluoromethyl)ethyl sulfamate In dichloromethane at 30℃; for 8h;	88%
With 4-methyl-morpholine; sulphamoyl chloride In di-isopropyl ether; N,N-dimethyl-formamide at 5℃; for 1h; Product distribution / selectivity; Crude product recrystalization;	76%
With sulphamoyl chloride; triethylamine In di-isopropyl ether; N,N-dimethyl acetamide at 5℃; for 1h; Product distribution / selectivity; Crude product recrystalization;	75%

: N-benzyloxycarbonyl-2,3: 4,5-di-O-(1-methylethylidene)-β-D-fructopyranosaminosulfonates potassium salt

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With palladium on activated charcoal In methanol at 20℃; under 9000.9 Torr; for 3h;	83%

: N-[(diphenylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With water; sodium acetate; acetic acid In acetone at 68 - 70℃; for 1 - 1.5h; pH=3.5; Product distribution / selectivity; Heating / reflux;	67%
With sodium acetate; acetic acid In water; acetone at 68 - 70℃; for 1 - 1.5h; pH=3.5; Product distribution / selectivity; Heating / reflux;	67%
With water In acetone at 70℃; for 2h; pH=3.5; aq. acetate buffer;

: N-{[methyl(phenyl)amino]carbonyl}-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With water; sodium acetate; acetic acid In acetone at 70℃; for 2 - 2.5h; pH=3.5; Product distribution / selectivity; Heating / reflux;	63%
With sodium acetate; acetic acid In water; acetone at 70℃; for 2 - 2.5h; pH=3.5; Product distribution / selectivity; Heating / reflux;	63%

: 876403-98-4
N-[(diethylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
Stage #1: N-[(diethylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate With sodium hydroxide; water; acetic acid In acetone at 78 - 79℃; for 1 - 8.5h; pH=2.5 - 5; Heating / reflux; Stage #2: With sodium hydroxide In water; acetone Product distribution / selectivity;	61%
With sodium hydroxide; acetic acid In water; acetone at 78 - 79℃; for 1 - 8.5h; pH=2.5 - 5.0; Product distribution / selectivity; Heating / reflux;	61%
With water; sodium acetate; acetic acid In acetonitrile at 80℃; for 1.5 - 2h; pH=3.5; Product distribution / selectivity;

: 106881-41-8
2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate

: 122-51-0
orthoformic acid triethyl ester

: 433-27-2
Trifluoroacetaldehyde ethyl hemiacetal

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With sulfuric acid	30%

...Expand

: 106881-35-0
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In ethyl acetate under 2844.39 - 3102.97 Torr; for 8h;

: 2,2,7,7,-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b,4',5'-d]pyran-3a-ylmethyl (E)-benzylidenesulfamate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With hydrogenchloride; water In acetone at 20℃; for 1.5h; Product distribution / selectivity;

: 627538-01-6
N-(2-methoxycarbonylphenyl)carbonyl-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With sodium hydroxide In DMF (N,N-dimethyl-formamide) at 20 - 80℃; for 12h; Product distribution / selectivity;

: N-phenoxycarbonyl-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

: 97240-79-4
topiramate

Conditions

Conditions	Yield
With hydrogen; palladium on activated carbon In ethanol at 20℃; under 2585.81 Torr; for 5h; Product distribution / selectivity;

topiramate base: topiramate base

: 97240-79-4
topiramate

Conditions

Conditions	Yield
In water; acetone at 0 - 35℃; Purification / work up;

: 57-48-7
D-Fructose

: 97240-79-4
topiramate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid 2: SULFAMIDE; pyridine / 5,5-dimethyl-1,3-cyclohexadiene / 130 - 140 °C View Scheme

: 7660-25-5
D-fructose

: 97240-79-4
topiramate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc(II) chloride / 2 h / 58 °C 2: sulfuryl dichloride; 1H-imidazole / dichloromethane / 2.5 h / 0 °C / Molecular sieve 3: ammonia / ethanol / 6 h / 20 °C / Green chemistry; Industrial scale View Scheme

: 6347-01-9
fructopyranose

: 97240-79-4
topiramate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / acetone / 0 - 15 °C / Inert atmosphere; Large scale 2: sulfuryl dichloride; pyridine / dichloromethane; toluene / 3 h / -10 - 20 °C 3: ammonia / tetrahydrofuran; hexane / 3 h / 20 °C View Scheme

: 97240-79-4
topiramate

: 106881-35-0
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose azidosulfate

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.0833333h;	99%

: 4641-57-0
1-phenylpyrrolidin-2-one

: 97240-79-4
topiramate

: ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl ((E)-1-phenylpyrrolidin-2-ylidene)sulfamate

Conditions

Conditions	Yield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;	98%

: 67-56-1
methanol

: 97240-79-4
topiramate

: 106881-46-3, 106881-47-4
methyl D-fructopyranoside sulfamate

Conditions

Conditions	Yield
With hydrogenchloride at 23℃; for 24h;	94%

: 75-03-6
ethyl iodide

: 97240-79-4
topiramate

: N-ethyl topiramate

Conditions

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 48h;	88%

: 3130-75-4
4-phthalimidobutyric acid

: 97240-79-4
topiramate

: C24H30N2O11S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	88%

: 97240-79-4
topiramate

: 74-88-4
methyl iodide

: 97240-80-7
2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose methylsulfamate

Conditions

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 48h;	86%

: 97240-79-4
topiramate

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: C15H26N2O8S

Conditions

Conditions	Yield
With thionyl chloride In chloroform at 60℃; for 3h;	80%

: 2466-76-4
N-Acetylimidazole

: 97240-79-4
topiramate

: Acetyl-sulfamic acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester; compound with 1H-imidazole

Conditions

Conditions	Yield
In toluene for 7h; Heating;	78%

: 107-08-4
1-iodo-propane

: 97240-79-4
topiramate

: N-propyl topiramate

Conditions

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 48h;	77%

: 100-39-0
benzyl bromide

: 97240-79-4
topiramate

A: N,N'-dibenzyl topiramate

B: N-benzyl topiramate

Conditions

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 36h;	A 7% B 77%

...Expand

: 108-86-1
bromobenzene

: 97240-79-4
topiramate

: 106881-36-1
((3aR,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl phenylsulfamate

Conditions

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 30℃; for 24h; Inert atmosphere; Irradiation; Sealed tube;	73%

: 97240-79-4
topiramate

: 589-15-1
1-bromomethyl-4-bromobenzene

A: N-(4-bromobenzyl)topiramate

B: N,N-di(4-bromobenzyl)topiramate

Conditions

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 36h;	A 68% B 11%

...Expand

: 97240-79-4
topiramate

: 1765-40-8
(bromomethyl)pentafluorobenzene

A: C19H22F5NO8S

B: N,N-di(pentaflourobenzyl)topiramate

Conditions

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 80℃; for 36h;	A 64% B 28%

...Expand

: 128-13-2
ursodeoxycholic acid

: 97240-79-4
topiramate

: C36H59NO11S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 6h;	60%

: 623-73-4
diazoacetic acid ethyl ester

: 97240-79-4
topiramate

: 103-84-4
Acetanilid

: ethyl N-phenyl-N-((E)-1-(((((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methoxy)sulfonyl)imino)ethyl)glycinate

Conditions

Conditions	Yield
With zinc trifluoromethanesulfonate In cyclohexane at 90℃; for 12h;	57%

...Expand

: 97240-79-4
topiramate

: 70-11-1
α-bromoacetophenone

A: C20H27NO9S

B: C28H33NO10S

Conditions

Conditions	Yield
With potassium fluoride on basic alumina	A 54% B 33%

...Expand

: 3618-96-0
(S)-N-acetylphenylalanine

: 97240-79-4
topiramate

: methyl (1-(((((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methoxy)sulfonyl)imino)ethyl)-L-phenylalaninate

Conditions

Conditions	Yield
With diazoacetic acid ethyl ester; manganese(II) perchlorate hexahydrate In cyclohexane at 90℃; for 12h; chemoselective reaction;	48%

: 6651-36-1
1-(Trimethylsilyloxy)cyclohexene

: 97240-79-4
topiramate

: 106881-40-7
4,5-O-cyclohexylidene-2,3-O-(1-methyl-ethylidene)-β-D-fructopyranose sulfamate

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran for 0.0833333h;	43%

: 97240-79-4
topiramate

: 3,6-dioxa-2-thia-1-azaspiro<4.5>decane-8α,9α,10β-triol 2,2-dioxide

Conditions

Conditions	Yield
With Amberlite IR-45 (anion-exchange resin, hydroxide form); trifluoroacetic acid for 18h; Ambient temperature;	43%

: 97240-79-4
topiramate

: 106881-41-8
2,3-O-(1-Methylethylidene)-β-D-fructopyranose 1-sulfamate

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 45℃; for 3.5h;	31%

: 633-65-8
berberine chloride

: 97240-79-4
topiramate

: C31H35N2O11S(1+)*Cl(1-)

Conditions

Conditions	Yield
In ethanol for 16h; Reflux;	20%

Topiramate Specification

1. Introduction of Topiramate

Topiramate, with the systematic name of beta-D-Fructopyranose, 2,3:4,5-bis-O-(1-methylethylidene)-, sulfamate, is one kind of white powder. This chemical belongs to the Product Categories which include Active Pharmaceutical Ingredients; APIs; Health & Beauty; Carbohydrates & Derivatives; Pharmaceuticals; Glutamate receptor. It is used as an anticonvulsant and an antidepressant. It is also used to treat Post Traumatic Stress Disorder.

2. Properties of Topiramate

Topiramate has the properties: (1)Molecular Formula: C12H21NO8S; (2)Molecular Weight: 339.362040 g/mol; (3)Index of Refraction: 1.497; (4)Molar Refractivity: 74.32 cm³; (5)Molar Volume: 253.8 cm³; (6)Surface Tension: 53.3 dyne/cm; (7)Density: 1.336 g/cm³; (8)Flash Point: 219.1 °C; (9)Enthalpy of Vaporization: 69.55 kJ/mol; (10)Boiling Point: 438.7 °C at 760 mmHg; (11)Vapour Pressure: 6.76E-08 mmHg at 25 °C; (12)Melting Point: 125°C ; (13)DMSO Solubility : ~44 mg/mL; (14)Storage Temp.: 2-8°C.

3. Toxicity of Topiramate

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	intraperitoneal	> 1500mg/kg (1500mg/kg)		Drugs of the Future. Vol. 14, Pg. 342, 1989.

4. Safety Information of Topiramate

Safety Information of Topiramate (CAS NO. 97240-79-4):
Hazard Codes: Xi Irritant
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36:Wear suitable protective clothing
WGK Germany: 3
RTECS: LS7083000

Product Name

Topiramate

Synthetic route

Topiramate Specification

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